I would say Jeno's Steaks on B&A Blvd,downtown Severna Park. By far the best cheesesteaks in Maryland. Annapolis used to have a great place called Freds Tiffany Room,but it closed a few years back.Now the city just seems to get more expensive and touristy.There are still some good places like Lewnes Steak House but the prices are high.

+1 for either (or both) Galway Bay and Chick & Ruth's, both of which are very close to the city dock area. If your belly's too full from Chick & Ruth's you can sleep it off upstairs in the Scottlar Inn.